Fall/Winter
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How to Wear Shorts for Fall

Welcome back to our 26 Days of Fall Outfits series! Today I’m styling fall outfit with shorts.

26 Days of Fall Outfits: How to Wear Shorts for Fall

For those in warmer climates, the weather may not get cold until holiday time. Here in Pennsylvania, it’s still warm most days in early September, so one way I like to make the seasonal transition is by wearing shorts with long sleeves or a jean jacket. I also recommend switching out your usual sandals for ballet flats instead.

Let’s talk about shorts for a minute. I know not all women are comfortable wearing shorts. You definitely have to consider your age and body type. The shorts I’m wearing in this post are the Ann Taylor City Shorts (and they’re currently ON SALE!) I have them in a few styles, and I really like them, but I know they’re shorter than some are comfortable with. These have a 4-1/2 inch inseam.

26 Days of Fall Outfits: How to Wear Shorts for Fall

If you like a slightly longer length, these Metro Shorts are nice too (and also on sale). They have a 6-inch inseam, which is probably best for most women. You can always do a Bermuda-length short if you’re older or aren’t comfortable showing that much leg.

For more information, you might like my Shorts for Moms post. Although it is a year old, the information on styles and fit is relevant, and I did update the shopping links not too long ago.

I am loving my leopard flats right now. I’ve actually had to force myself not to wear them with every fall outfit I’ve styled so far! You can treat leopard like a neutral so it goes with practically everything, and it definitely elevates an outfit.

26 Days of Fall Outfits: Shorts with Ballet Flats and Jean Jacket

I picked up these Alaine Scalloped Topline Flats on the Nordstrom Anniversary sale when they were 30% off. They’re back to regular price now, and while I love them, I like these Felicia Flats even better.

leopard flats

At full price, they’re only $10 apart (the Felicia wasn’t included in the sale, thus, my choice of the Alaine) but the Felicia flats actually have a padded sole, which makes them more comfortable. I checked them out the last time I was at Nordstrom. They get amazing ratings on the website too. I do like the scalloped detail on the Alaine, but all things being equal, I’d go for comfort.

If you’re looking for a budget option, Target has these and these.

leopard ballet flats

For this outfit, I carried my light brown bucket bag and accessorized with some of my favorite Stella & Dot jewels. (I’m a Stella & Dot stylist, for those not in-the-know!)

26 Days of Fall Outfits: Shorts with Ballet Flats and Jean Jacket

If you wanted it to look more fallish, you could wear a top and/or shorts in earth tones, but this works well for these early days in September when most people are still wearing their summer clothes.

26 Days of Fall Outfits: How to Wear Shorts for Fall

Outfit Details: jean jacket (similar here and here) | V-Neck tee | Ann Taylor City Shorts | Sam Edelman Alaine Scalloped Leopard Flats (budget option) | FitBit bracelet | R Bracelet | Coral Cay Earrings (sold out; similar) | Signature Engravable Disk Necklace | Lexi Bucket Bag (now only in black)

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28 thoughts on “How to Wear Shorts for Fall

  1. I’m new to your blog and really love it. I also read Cyndi’s blog, of Grace and Beauty. I am really enjoying your fall outfits and truly appreciate the both of you! God Bless!!!!????

  2. I’ll have to check out those shorts, although fall weather has hit with a vengeance, here, so I’m actually wearing jeans sometimes. Doesn’t it feel weird to put them on for the first time again? 🙂

    You look so stinkin’ cute in this outfit. Really like that bag, too. And the shoes.

    Question: I’ve avoided a jean jacket because I wear jeans so often. Do you mix your denims (obviously, I’m not talking about white, but the blues and blacks)?

    Thanks, as always for the great tips.

    1. Yeah, it’s hot here still! I do wear jeans all summer, though. I just love them too much to put them away. 🙂

      I do not mix denims. It’s actually very trendy and of the moment, but I haven’t found a combination that I love. I would do it maybe if I had the right combo. I think it has to be done intentionally or it looks like a fashion emergency. LOL I tend to shy away from anything that might be construed as a fashion emergency, ha!

  3. I got a pair of the Felicia flats and LOVE them. I got Sterling which are a beautiful gray. I wore them last week when I was my feet for 12 hours at a conference and they were perfect. Comfortable and stylish. I walked several mile in them around DC as well in them and didn’t pay my feet a moments notice. I think that they are the perfect choice if you need both comfort and style. I am going to be buying another pair (or two)

      1. I like Sterling because it isn’t totally solid so it’s more dressy. Its multitoned gray/silver. Check that one out, you might like it. I’m probably buying the Saddlepair one as well.

  4. Love both of those shoes but held off buying them worrying about support. I found these this weekend and am in love! http://bit.ly/1Xg6fNE. They have great arch support and a sturdy bottom so hopeful they hold up better than most ballet type flats.

  5. Good Morning! Love your outfit! I love wearing a denim jacket in the fall, course I’m one that is to old for shorts. But if I could…I would! Lol!! And I LOVE the leopard flats, need to find a store to try them on. Have a great day J-Lynne! Love you & Cyndi!!

  6. I’m in mourning over the Lexi bag. (Sniff!) It’s my own fault though. I really wanted the one in Cuoio but procrastinated. I really love that color for summer into fall. Style too because it isn’t a HUGE bucket bag and at 5′ 1″ I can’t do a huge bag. Now, it’s gone.

    I may have to console myself with some cute shoes. 🙂

      1. You know, I didn’t even think of that. Nothing against eBay, but I might be concerned about not getting an authentic piece. I will browse around though. Thanks for the tip!

  7. I’m new to your blog, but have followed Cyndi for sometime now. I’m really not ready to give up summer, but enjoy transitioning my clothes into fall. I really like how you added the denim jacket and leopard print flats with your shorts-perfection!! I’m looking forward to seeing more!

  8. Here in the south, shorts and capris will still be worn in September. I’m glad you included them.

    Love the shoes – pretty and versatile. My favorite part of this outfit is the zippered jean jacket! I would love to have one – but they are hard to find.

      1. It was made so you could wear it that way. For instance, the key on the zipper flips around so it’s accessible if you do. CAbi is famous for fabulous details. 🙂

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